1. Field of the Invention
The present invention relates to novel organosilicon compounds and a process for the preparation of organosilicon compounds.
2. Description of Related Art
Alkenylsilanes may be converted into silanes having various structures by utilizing their C.dbd.C double bond as well as they may be utilized as a unique reaction of a vinyl silane for synthesis of a stereospecific olefin, an .alpha.,.beta.-unsaturated carbonyl compound as well as a stereospecific alcohol or .alpha.-oxycarbonyl compound. They are extremely useful for intermediates for organic synthesis or for raw materials for physiologically active substances. Alkylsilanes are also useful as intermediate substances for organic synthesis and raw materials for synthesis of physiologically active substances. Their uses are disclosed in Synthesis, 1979, 761; E. W. Colvin: "Silicon in Organic Synthesis", Butterworths (1981); W. P. Weber: "Silicon Reagents for Organic Synthesis", Springer (1983), etc.
Further, bis(silyl)alkanes are used as intermediate substances for organic synthesis and for synthesis of physiologically active substances and they are polymerized into polycarbosilanes which are useful as photo-degradable polymers, resist materials having a high resistance to oxygen plasma, precursors for silicon carbide, and so on.
The alkenylsilanes are conventionally prepared as follows:
(1) by hydrosilylating an acetylene with a hydrosilane in the presence of a catalyst; PA0 (2) by converting an acetylene into a metal acetylide and reacting the metal acetylide with a halosilane followed by reducing the resulting silyl acetylene; PA0 (3) converting an alkenyl halide into an alkenyl metal compound which, in turn, is reacted with a halosilane; PA0 (4) reacting an alkenyl halide with a silyl alkali metal. PA0 (5) by hydrosilylating olefins with a hydrosilane in the presence of a catalyst; and PA0 (6) by reacting an alkali metal compound with a halosilane. PA0 (7) by reacting a compound having an acetylenic, unsaturated bond, C.tbd.C, with a compound having a Si--Si bond in the presence of a catalyst to thereby give a compound having a Si--C.dbd.C--Si bond which, in turn, is hydrogenated; and PA0 (8) by reacting the vinylsilane prepared in the procedures (1) to (4) above with a hydrosilane in the presence of a catalyst. PA0 wherein R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyloxy group, an N,N-dialkylamino group, fluorine atom, bromine atom or chlorine atom, and may link with each other to form a cyclic structure, PA0 wherein R.sup.1, R.sup.2 and R.sup.3 are each hydrogen atom, an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an aralkyl group, an aryl group, an aromatic heterocyclic group, an alkoxycarbonyl group, a cyano group, an N,N-dialkylaminocarbonyl group, an alkoxy group, an N,N-dialkylamino group, an N-alkyl-N-acylamino group or an N,N-diacylamino group, and may link with each other to form a cyclic structure, PA0 wherein R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are each an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyloxy group, an N,N-dialkylamino group, fluorine atom, bromine atom or chlorine atom, and may link with each other to form a cyclic structure, PA0 A.sup.1 and A.sup.3 are each an alkyl group, and may link with each other to form a cyclic structure; PA0 A.sup.2 and A.sup.4 are each an alkoxy group and an aryl group; and PA0 m and n are each 0 or an integer from 1 to 3. PA0 A is an alkylene group or a cycloalkylene group, each forming a four-membered or five-membered cycle. PA0 A.sup.5, A.sup.6, A.sup.7, A.sup.8, A.sup.9 and A.sup.10 are identical to or different from each other and are each an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, an alkoxy group, an acyloxy group, an N,N-dialkylamino group, fluorine atom, bromine atom or chlorine atom, and may link with each other to form a cyclic structure; PA0 A.sup.11 is an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an aralkyl group, an aryl group, an aromatic heterocyclic group, an alkoxycarbonyl group, a cyano group, an N,N-dialkylaminocarbonyl group, an alkoxy group, an N,N-dialkylamino group, an N-alkyl-N-acylamino group or an N,N-diacylamino group.
The alkylsilanes may be prepared by the following conventional procedures:
Furthermore, the bis(silyl)alkanes may be conventionally prepared as follows:
Those conventional procedures present various disadvantages and are said to be insufficient in various respects. The conventional processes as referred to as (1), (2) and (7) above use the acetylene as a raw material, which is so expensive and apt to be explosive that they accompany the difficulty in preparing on an industrial scale. The processes (1), (5) and (8) use the hydrosilane which is also expensive so that they are industrially disadvantageous. For the processes (2), (3), (4) and (6), there are used the alkali metal compounds or magnesium reagents which are also expensive as well as which may be encountered with dangers in use and which is so highly reactive that they may present the problem with protection over functional groups of the resulting compounds. Furthermore, the processes (2), (3), (4), (6), (7) and (8) are each a multi-step process which is remote from the end step.